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EP0852499A4 - Therapeutic azide compounds - Google Patents

Therapeutic azide compounds

Info

Publication number
EP0852499A4
EP0852499A4 EP96932197A EP96932197A EP0852499A4 EP 0852499 A4 EP0852499 A4 EP 0852499A4 EP 96932197 A EP96932197 A EP 96932197A EP 96932197 A EP96932197 A EP 96932197A EP 0852499 A4 EP0852499 A4 EP 0852499A4
Authority
EP
European Patent Office
Prior art keywords
drugs
azide
therapeutic
amine
azide derivatives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96932197A
Other languages
German (de)
French (fr)
Other versions
EP0852499B1 (en
EP0852499A1 (en
Inventor
Chung K Chu
Lakshimi Kotra
Kostantin Manouilov
Jinfa Du
Raymond Schinazi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Emory University
University of Georgia Research Foundation Inc UGARF
Original Assignee
Emory University
University of Georgia Research Foundation Inc UGARF
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Emory University, University of Georgia Research Foundation Inc UGARF filed Critical Emory University
Publication of EP0852499A1 publication Critical patent/EP0852499A1/en
Publication of EP0852499A4 publication Critical patent/EP0852499A4/en
Application granted granted Critical
Publication of EP0852499B1 publication Critical patent/EP0852499B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/52—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an inorganic compound, e.g. an inorganic ion that is complexed with the active ingredient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Pharmaceutical prodrug compositions are provided comprising azide derivatives of drugs which are capable of being converted to the drug in vivo. Azide derivatives of drugs having amine, ketone and hydroxy substituents are converted in vivo to the corresponding drugs, increasing the half-life of the drugs. In addition azide prodrugs are often better able to penetrate the blood-brain barrier than the corresponding drugs. Especially useful are azide derivatives of cordycepin, 2'-F-ara-ddI, AraA, acyclovir, penciclovir and related drugs. Useful azide prodrugs are azide derivatives of therapeutic alicyclic amines, ketones, and hydroxy-substituted compounds, including aralkyl, heterocyclic aralkyl, and cyclic aliphatic compounds, where the amine or oxygen moiety is on the ring, or where the amine or oxygen moiety is on an aliphatic side chain, as well as therapeutic purines and pyrimidines, nucleoside analogs and phosphorylated nucleoside analogs.
EP96932197A 1995-09-07 1996-09-06 Therapeutic azide compounds Expired - Lifetime EP0852499B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US338395P 1995-09-07 1995-09-07
US3383 1995-09-07
PCT/US1996/014494 WO1997009052A1 (en) 1995-09-07 1996-09-06 Therapeutic azide compounds

Publications (3)

Publication Number Publication Date
EP0852499A1 EP0852499A1 (en) 1998-07-15
EP0852499A4 true EP0852499A4 (en) 2001-03-07
EP0852499B1 EP0852499B1 (en) 2010-03-03

Family

ID=21705613

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96932197A Expired - Lifetime EP0852499B1 (en) 1995-09-07 1996-09-06 Therapeutic azide compounds

Country Status (9)

Country Link
US (2) US6271212B1 (en)
EP (1) EP0852499B1 (en)
JP (1) JPH11512397A (en)
AT (1) ATE459361T1 (en)
AU (1) AU709345B2 (en)
BR (1) BR9610120A (en)
CA (1) CA2231442A1 (en)
DE (1) DE69638137D1 (en)
WO (1) WO1997009052A1 (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE459361T1 (en) * 1995-09-07 2010-03-15 Univ Georgia THERAPEUTIC AZIDE COMPOUNDS
ATE321561T1 (en) * 1998-11-05 2006-04-15 Centre Nat Rech Scient ACIDO DERIVATIVES OF BETA-L-2'-NUCLEOSIDES FOR HIV INFECTION TREATMENT
ATE315574T1 (en) 1998-11-05 2006-02-15 Centre Nat Rech Scient NUCLEOSIDES WITH ANTI-HEPATITIS B VIRUS EFFECT
US6407077B1 (en) 1998-11-05 2002-06-18 Emory University β-L nucleosides for the treatment of HIV infection
EP1964569A3 (en) 2000-04-13 2009-07-22 Pharmasset, Inc. 3'-or 2'-hydroxymethyl substituted nucleoside derivatives for treatment of viral infections
MY164523A (en) 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
AP2006003708A0 (en) 2000-05-26 2006-08-31 Idenix Cayman Ltd Methods and compositions for treating flavivirusesand pestiviruses
RS113904A (en) * 2002-06-28 2007-02-05 Idenix (Cayman) Limited 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
NZ537662A (en) 2002-06-28 2007-10-26 Idenix Cayman Ltd 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7608600B2 (en) 2002-06-28 2009-10-27 Idenix Pharmaceuticals, Inc. Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
ES2624353T3 (en) 2002-11-15 2017-07-13 Idenix Pharmaceuticals Llc 2'-Methyl nucleosides in combination with interferon and Flaviviridae mutation
AU2003293404A1 (en) * 2002-12-03 2004-06-23 Baylor University Compounds resistant to metabolic deactivation and methods of use
ES2470771T3 (en) 2002-12-12 2014-06-24 Idenix Pharmaceuticals, Inc Procedure for the production of branched nucleosides in 2 '
EP1745573A4 (en) * 2003-03-20 2010-05-26 Microbiol Quimica Farmaceutica Methods of manufacture of 2 -deoxy- beta-l-nucleosides
US7718684B2 (en) * 2004-02-24 2010-05-18 The Regents Of The University Of California Methods and materials for assessing prostate cancer therapies and compounds
CN101068577A (en) * 2004-10-07 2007-11-07 皇家飞利浦电子股份有限公司 Use of the staudinger ligation in imaging and therapy end kits for imaging and therapy
JP4516863B2 (en) * 2005-03-11 2010-08-04 株式会社ケンウッド Speech synthesis apparatus, speech synthesis method and program
KR101288729B1 (en) * 2005-04-01 2013-07-23 인터자인 테크놀로지스, 인코포레이티드 Polymeric micelles for drug delivery
US7709517B2 (en) 2005-05-13 2010-05-04 The Regents Of The University Of California Diarylhydantoin compounds
JP2009512642A (en) * 2005-10-04 2009-03-26 コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ Staudinger reaction in imaging and therapy and kits used for imaging and therapy
EP1976382B1 (en) 2005-12-23 2013-04-24 IDENIX Pharmaceuticals, Inc. Process for preparing a synthetic intermediate for preparation of branched nucleosides
EP2013187B1 (en) 2006-03-29 2014-10-29 The Regents of The University of California Diarylthiohydantoin compounds
AR069039A1 (en) * 2007-10-26 2009-12-23 Univ California DIARILHIDANTOINE COMPOUNDS, PHARMACEUTICAL COMPOSITION, COMPOUND OBTAINING PROCESS, USEFUL FOR HYPERPROLIFERATIVE DISORDERS
US10351918B2 (en) 2013-10-30 2019-07-16 Green Life Biotech, Llc Pathogenesis quantification systems and treatment methods for citrus greening blight
CN103772460B (en) * 2014-02-14 2016-02-10 江苏省中国科学院植物研究所 The extraction process of cordycepin in silkworm Chinese caterpillar fungus
GB201718804D0 (en) * 2017-11-14 2017-12-27 Nuclera Nucleics Ltd Novel use
US11279981B2 (en) 2018-09-24 2022-03-22 University Of South Florida Biomarkers of low grade glioma and pediatric neuroblastoma

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0145207A1 (en) * 1983-10-31 1985-06-19 Warner-Lambert Company Purine derivatives
EP0400686A1 (en) * 1985-09-24 1990-12-05 Hoechst Aktiengesellschaft 2-Amino-9-[1,3bis-(isopropoxy)-propyl-2-oxymethyl]-purine, its utilization and medicaments containing it

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4724232A (en) * 1985-03-16 1988-02-09 Burroughs Wellcome Co. Treatment of human viral infections
US5180824A (en) * 1990-11-29 1993-01-19 Berlex Biosciences Inc. 6-azido-2-fluoropurine, useful in the synthesis of nucleosides
US5602246A (en) * 1992-11-25 1997-02-11 Schering Aktiengesellschaft Process for the preparation of fludarabine or fludarabine phosphate from guanosine
US5457187A (en) * 1993-12-08 1995-10-10 Board Of Regents University Of Nebraska Oligonucleotides containing 5-fluorouracil
ATE459361T1 (en) * 1995-09-07 2010-03-15 Univ Georgia THERAPEUTIC AZIDE COMPOUNDS

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0145207A1 (en) * 1983-10-31 1985-06-19 Warner-Lambert Company Purine derivatives
EP0400686A1 (en) * 1985-09-24 1990-12-05 Hoechst Aktiengesellschaft 2-Amino-9-[1,3bis-(isopropoxy)-propyl-2-oxymethyl]-purine, its utilization and medicaments containing it

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HAKIMELAHI, G. H. ET AL: "The role of chloromethyl ethers in the formation of N(7)- and N(9)-alkylated isomers of adenine. Synthesis of 2-[9- (ethoxymethyl)adenyl]phosphonate", J. SCI., ISLAMIC REPUB. IRAN (1990), 1(3), 192-6, XP000978246 *
KOJIMA, EIJI ET AL: "Synthesis and structure-activity relationships of 2',3'-dideoxypurine nucleosides as potential antiretroviral agents", NUCLEIC ACIDS SYMP. SER. (1991), 25(SYMP. NUCLEIC ACIDS CHEM., 18TH, 1991), 91-2, XP000978242 *
KOUDRIAKOVA, TANYA ET AL: "In Vitro and in Vivo Evaluation of 6-Azido-2',3'-dideoxy-2'-fluoro-.beta.-D-arabinofuranosylpurine and N6-Methyl-2',3'-dideoxy-2'- fluoro-.beta.-D-arabinofuranosyladenine as Prodrugs of the Anti-HIV Nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI", J. MED. CHEM. (1996), 39(23), 4676-4681, XP000971766 *

Also Published As

Publication number Publication date
AU7107696A (en) 1997-03-27
BR9610120A (en) 1999-12-21
US6271212B1 (en) 2001-08-07
US20010036930A1 (en) 2001-11-01
WO1997009052A1 (en) 1997-03-13
AU709345B2 (en) 1999-08-26
US6949521B2 (en) 2005-09-27
JPH11512397A (en) 1999-10-26
ATE459361T1 (en) 2010-03-15
DE69638137D1 (en) 2010-04-15
EP0852499B1 (en) 2010-03-03
EP0852499A1 (en) 1998-07-15
CA2231442A1 (en) 1997-03-13

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